Psoralen Photochemistry and Nucleic Acid Structure
Open accessAbstract
Many new psoralen derivatives have been synthesized in an effort to enhance their water solubility and their binding to nucleic acids. Availability of the very soluble strongly binding compounds has improved our abilities to follow the optical changes associated with the photochemistry of psoralens with DNA. Changes in both absorbance and fluorescence are presented in this review. A kinetic model for the photochemistry concludes that the detailed kinetics is dominated by the equilibrium constant for intercalation of the psoralen in the DNA, the quantum yield for photoaddition to DNA once intercalated and the quantum yield for photodestruction of the drug in water. With these 3 parameters the kinetics of photochemistry is predictable. The values of these parameters for numerous derivatives of 8-methoxypsoralen and 4,5',8 trimethylpsoralen are presented. Application of this photochemistry to a study of nucleic acid secondary structure in chromatin, fd bacteriophage, and in ribosomes is reviewed.
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Furocoumarin derivatives undergo [2+2] photocycloaddition to the 5,6-double bond of thymidine, which is the major target of these oxygen-independent photoreactions.
“Major mechanistic insights into the mechanisms of [2+2] photocycloaddition of furocoumarin derivatives to the 5,6-double bond of thymidine, the major target of these oxygen-independent photoreactions, have been gained from extensive model studies (35,(161)(162)(163).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [161]
UVA excitation of furan-side monoadducts can form DNA interstrand cross-links through cycloaddition to opposite thymine at 5'-TpA-3' sequences.
“While pyrone-side monoadducts to thymine are not photoreactive, UVA excitation of furan-side monoadducts may lead to the formation of harmful DNA interstrand cross-links (ICLs) through cycloaddition to opposite thymine at 5¢-TpA-3¢ sequences (Fig. 7) that are the preferential sites of photoreactions of most psoralen derivatives (35,(161)(162)(163).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [161]
Two types of monoadducts are formed as pairs of diastereomers through the 4',5'-double bond of the furan moiety or the 3,4-ethylenic bond of the pyrone ring.
“Essentially, the formation of two types of monoadducts as pairs of diastereomers through the implication of either the 4¢,5¢-double bond of the furan moiety or the 3,4-ethylenic bond of the pyrone ring has been reported.”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [161]
Pyrone-side monoadducts to thymine are not photoreactive.
“While pyrone-side monoadducts to thymine are not photoreactive, UVA excitation of furan-side monoadducts may lead to the formation of harmful DNA interstrand cross-links (ICLs) through cycloaddition to opposite thymine at 5¢-TpA-3¢ sequences (Fig. 7) that are the preferential sites of photoreactions of most psoralen derivatives (35,(161)(162)(163).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [161]
5'-TpA-3' sequences are the preferential sites of photoreactions of most psoralen derivatives.
“While pyrone-side monoadducts to thymine are not photoreactive, UVA excitation of furan-side monoadducts may lead to the formation of harmful DNA interstrand cross-links (ICLs) through cycloaddition to opposite thymine at 5¢-TpA-3¢ sequences (Fig. 7) that are the preferential sites of photoreactions of most psoralen derivatives (35,(161)(162)(163).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [161]
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Cites
Isaacs, S. T., Shen, C.-K. J., Hearst, J. E., & Rapoport, H. (1977) · Biochemistry · doi:10.1021/bi00625a005 · Cited by 309 · see citing works
Self-citationPHOTOREACTIONS AT 3655Å BETWEEN PYRIMIDINE BASES AND SKIN‐PHOTOSENSITIZING FUROCOUMARINS
Musajo, L., Bordin, F., Caporale, G., et al. (1967) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1967.tb08736.x · Cited by 220 · see citing works
PHOTOREACTIONS AT 3655 Å LINKING THE 3–4 DOUBLE BOND OF FUROCOUMARINS WITH PYRIMIDINE BASES
Musajo, L., Bordin, F., & Bevilacqua, R. (1967) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1967.tb09659.x · Cited by 145 · see citing works
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Self-citationPhotochemical Inactivation of DNA and RNA Viruses by Psoralen Derivatives
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Self-citationJohnston, B. H., Johnson, M., Moore, C. B., et al. (1977) · Science · doi:10.1126/science.887929 · Cited by 81 · see citing works
Psoralen-crosslinked secondary structure map of single-stranded virus DNA.
Shen, C.-K. J., & Hearst, J. E. (1976) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.73.8.2649 · Cited by 70 · see citing works
Self-citationBase-pairing between distant regions of the Escherichia coli 16 S ribosomal RNA in solution
Wollenzien, P. L., Hearst, J. E., Thammana, P., et al. (1979) · Journal of Molecular Biology · doi:10.1016/0022-2836(79)90351-6 · Cited by 57 · see citing works
Self-citationHearst, J. E., & Thiry, L. (1977) · Nucleic Acids Research · doi:10.1093/nar/4.5.1339 · Cited by 54 · see citing works
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Thompson, J. F., Wegnez, M. R., & Hearst, J. E. (1981) · Journal of Molecular Biology · doi:10.1016/0022-2836(81)90493-9 · Cited by 36 · see citing works
Self-citationShen, C. ‐. J., & Hearst, J. E. (1977) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.74.4.1363 · Cited by 36 · see citing works
Self-citationLow-level psoralen-deoxyribonucleic acid crosslinks induced by single laser pulses
Johnston, B. H., & Hearst, J. E. (1981) · Biochemistry · doi:10.1021/bi00507a012 · Cited by 28 · see citing works
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Self-citationTHE SITE OF TRIMETHYLPSORALEN CROSS-LINKING IN CHROMATIN
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Research works printed but not linked: 5
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Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup>
Cadet, J., Mouret, S., Ravanat, J., & Douki, T. (2012) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2012.01200.x · Cited by 300 · see citing works
- Authors
- Hearst, J. E.
- Affiliations
- University of California, Berkeley (US)
- Corresponding author
- Hearst, John E.
- Venue
- Journal of Investigative Dermatology
- Publisher
- Elsevier BV
- Published
- 1981-07
- Volume
- 77
- Issue
- 1
- Pages
- 39-44
- ISSN
- 0022-202X (ISSN-L)
- OpenAlex
- W1975879755
- Cited by
- 66
- References
- 22
- Citations by year
- 2025: 1 · 2024: 2 · 2023: 2 · 2022: 2 · 2021: 1 · 2020: 4 · 2018: 1 · 2017: 2 · 2016: 1 · 2015: 1 · 2013: 1 · 2012: 3
- FWCI
- 0.53
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Licence
- Locations
- Journal of Investigative Dermatology (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
- Physical Sciences › Materials Science › Materials Chemistry › Photochromic and Fluorescence Chemistry
- Keywords
- psoralen derivatives, DNA intercalation, nucleic acid secondary structure, 8-methoxypsoralen, 4,5',8-trimethylpsoralen, photodegradation kinetics, chromatin, bacteriophage fd, ribosome, fluorescence changes
- MeSH terms
- Antiviral Agents, DNA, Humans, Kinetics, Neoplasms, Nucleic Acids, Photochemistry, Phototherapy, Furocoumarins, Vaccines, Optics and Photonics
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